4-Toluenesulfonyl chloride → Cyclohexyl p-toluenesulfonate

HRID 1684327Notes

Reaction equation

HRID 1684327 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7966Cyclohexanol

Product 1

HCID 13722Cyclohexyl p-toluenesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round-bottomed flask (100 cc) was charged with cyclohexyl alcohol (5.01 9, 50.0 mmol) and p-toluenesulfonyl chloride (10.6 g, 55.6 mmol), followed by the addition of pyridine (20 mL) under ice cooling to form a solution. The solution was stirred for 8 h as it was warmed gradually to room temperature. After completion of the reaction, the reaction mixture was poured into ice water and stirred thoroughly. Following extraction with ether (50 mL×2), the organic layers were washed with 2N HCl, water and saturated brine and dried with anhydrous magnesium sulfate. After the desiccant was removed, the solvent was distilled off under vacuum to give cyclohexyl p-toluenesulfonate as a colorless clear oil (12.7 g; yield=99.0%). 1H-NMR(CDCl3,TMS,ppm): δ1.12-1.88(10H,m), 2.43(3H,s), 4.46(1H,m), 7.28(2H,d,J=8.9Hz), 7.76(2H,d,J=8.9Hz).

Workup

  1. customto form a solution
  2. customAfter completion of the reaction
  3. stirringstirred thoroughly
  4. extractionextraction with ether (50 mL×2)
  5. washthe organic layers were washed with 2N HCl, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter the desiccant was removed
  8. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-b30bf5716b3546b49897ecb11b9b30ca
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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